(3-Methylpyridin-2-yl)methanamine → Pyrimidine-4-carboxamide, 26

HRID 254154Notes

Reaction equation

HRID 254154 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1.[CH3:16][C:17]1[C:18]([CH2:23][NH2:24])=[N:19][CH:20]=[CH:21][CH:22]=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:24][CH2:23][C:18]2[C:17]([CH3:16])=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:10])[CH:5]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

4

Reactant 2

HCID 1514370(3-Methylpyridin-2-yl)methanamineHCID 287995992-Amino-6-(2-furyl)pyrimidine-4-carboxylic acid

Product 1

HCID 11220580Pyrimidine-4-carboxamide, 26Yield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-amino-6-(2-furyl)pyrimidine-4-carboxylic acid (206 mg, 1.0 mmol) in DMF (5 mL) was treated with N,N′-carbonyldiimidazole (162 mg, 1.0 mmol), stirred for 2 h, treated with 3-methylpyridine-2-methanamine (244 mg, 2.0 mmol), stirred for 2 h, poured onto water (50 mL) and extracted with EtOAc (2×25 mL). The extracts were washed with water, concentrated in vacuo, and the crude product was triturated with ether to give the title compound (109 mg, 35%) as a yellow solid.

Workup

  1. stirringstirred for 2 h
  2. additionpoured onto water (50 mL)
  3. extractionextracted with EtOAc (2×25 mL)
  4. washThe extracts were washed with water
  5. concentrationconcentrated in vacuo
  6. customthe crude product was triturated with ether

Sources & evidence

ORD record
ord-dfe8c1cc55d84b38ae4217bfa01c7d56
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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